Sodium Carbonate → HCID 178434687, compound

HRID 1671305Notes

Reaction equation

[CH3:1][C:2]1[C:3]([N:8]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[N:9]2)=[C:4]([OH:7])[NH:5][N:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:24]([CH3:35])[C:25]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=1[Cl:34])=[O:26].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[Cl:34][C:28]1[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]=1[C:25](=[O:26])[CH:24]([O:7][C:4]1[NH:5][N:6]=[C:2]([CH3:1])[C:3]=1[N:8]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:14])[F:15])=[N:9]1)[CH3:35]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 5′-methyl-3-trifluoromethyl-2′H-[1,4′]bipyrazolyl-3′-ol (Intermediate KA)(270 mg, 1.163 mmol) and cesium carbonate (379 mg, 1.163 mmol) in DMF (2.684 ml) at 50° C. is added 2-bromo-1-(2,4-dichloro-phenyl)-propan-1-one (Intermediate AA) (328 mg, 1.163 mmol) slowly in DMF (1.789 ml). The reaction is stirred at 50° C. for 1 hour before cooling to RT. 2M Na2CO3 (100 ml) is added and the crude product is extracted with EtOAc (2×100 ml). The organic phases are combined, washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product is purified by ISCO combiflash chromatography, eluting with 0 to 100% (iso-hexane/EtOAc) on a 24 g SiO2 column to give the title compound as a light brown oil; MS: m/z 433.24 [M+H]+

Workup

temperaturebefore cooling to RT
extractionthe crude product is extracted with EtOAc (2×100 ml)
washwashed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe crude product is purified by ISCO combiflash chromatography
washeluting with 0 to 100% (iso-hexane/EtOAc) on a 24 g SiO2 column

Sources & evidence

ORD record: ord-6f29bc0c909e4f778dc720fa7439080c
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994203B2

Reaction notes

Loading…